$41 Cheap flights to Middlesex County

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Top places to visit in Middlesex County

A coastal town with a lighthouse, houses, and a river.
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Old Saybrook

Old Saybrook

Cheap flights to Middlesex County from $41 One Way, $82 Round Trip

$82 return flights and $41 one-way flights to Middlesex County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 8 - Mon, Jan 11
RIC
Richmond
HVN
New Haven
$82 Roundtrip, found 19 hours ago
$82
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Richmond to New Haven, returning Mon, Jan 11, priced at $82 found 19 hours ago
Fri, Dec 4 - Mon, Dec 7
RIC
Richmond
HVN
New Haven
$87 Roundtrip, found 23 hours ago
$87
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Fri, Dec 4 from Richmond to New Haven, returning Mon, Dec 7, priced at $87 found 23 hours ago
Fri, Dec 11 - Mon, Dec 14
RIC
Richmond
HVN
New Haven
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 11 from Richmond to New Haven, returning Mon, Dec 14, priced at $92 found 1 day ago
Mon, Dec 7 - Thu, Dec 10
RIC
Richmond
BDL
Hartford
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Dec 7 from Richmond to Hartford, returning Thu, Dec 10, priced at $102 found 5 hours ago
Thu, Jan 21 - Sun, Jan 24
MCO
Orlando
HVN
New Haven
$123 Roundtrip, found 13 hours ago
$123
Roundtrip
found 13 hours ago
Select Avelo Airlines flight, departing Thu, Jan 21 from Orlando to New Haven, returning Sun, Jan 24, priced at $123 found 13 hours ago
Fri, Dec 11 - Mon, Dec 14
FLL
Fort Lauderdale
HVN
New Haven
$126 Roundtrip, found 19 hours ago
$126
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, Dec 11 from Fort Lauderdale to New Haven, returning Mon, Dec 14, priced at $126 found 19 hours ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando
HVN
New Haven
$128 Roundtrip, found 12 hours ago
$128
Roundtrip
found 12 hours ago
Select Avelo Airlines flight, departing Sat, Dec 5 from Orlando to New Haven, returning Sat, Dec 12, priced at $128 found 12 hours ago
Thu, Jan 7 - Sun, Jan 10
FLL
Fort Lauderdale
HVN
New Haven
$133 Roundtrip, found 17 hours ago
$133
Roundtrip
found 17 hours ago
Select Avelo Airlines flight, departing Thu, Jan 7 from Fort Lauderdale to New Haven, returning Sun, Jan 10, priced at $133 found 17 hours ago
Fri, Jan 8 - Tue, Jan 12
FLL
Fort Lauderdale
BDL
Hartford
$153 Roundtrip, found 5 days ago
$153
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Jan 8 from Fort Lauderdale to Hartford, returning Tue, Jan 12, priced at $153 found 5 days ago
Fri, Jan 22 - Mon, Jan 25
MCO
Orlando
BDL
Hartford
$168 Roundtrip, found 18 hours ago
$168
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Jan 22 from Orlando to Hartford, returning Mon, Jan 25, priced at $168 found 18 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCOEast HavenNovember 20 to November 23$143
FLLEast HavenNovember 21 to December 1$225
MCOWindsor LocksNovember 20 to November 27$264
SJUEast HavenNovember 20 to November 30$286
ATLEast HavenNovember 22 to December 6$292
SJUWindsor LocksNovember 22 to November 28$300
FLLWindsor LocksNovember 20 to November 23$325
TPAEast HavenNovember 20 to November 23$348
DENWindsor LocksNovember 20 to December 5$395
CLTWindsor LocksNovember 20 to November 22$399
TPAWindsor LocksNovember 20 to November 27$423
DCAWindsor LocksNovember 21 to November 28$429
ORDWindsor LocksNovember 20 to November 22$460
ATLWindsor LocksNovember 20 to November 24$476
LAXWindsor LocksNovember 22 to November 30$560
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Middlesex County Accommodation Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$82 nightly
The price is $95 total per night from Nov 15 to Nov 16
$95 total
Nov 15 - Nov 16
Total with taxes and fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowPier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $170 total per night from Nov 23 to Nov 24
$170 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowWater's Edge Resort & Spa
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
298 E Haddam Moodus Rd East Haddam CT
$167 nightly
The price is $192 total per night from Dec 14 to Dec 15
$192 total
Dec 14 - Dec 15
Total with taxes and fees
Stay at this cabin in East Haddam. Enjoy free parking and patios. Popular attractions Machimoodus State Park and Amasa Day House are located nearby.
9.4/10 Exceptional! (223 reviews)
"Everything was great just make sure you get there before it gets dark out. It’s relevantly hard to find the cabins in the pitch black. Overall the area was very quiet. We had neighbors but you really can’t hear anyone around you. It’s a great way to disconnect and unwind."

Reviewed on Nov 12, 2026

Opens in a new windowPostcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Dec 15 to Dec 16
$126 total
Dec 15 - Dec 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Mashantucket. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Foxwoods Resort Casino and ...
Opens in a new windowTwo Trees Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Middlesex County

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Bargain Flights to Middlesex County

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Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Middlesex County but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Middlesex County?
Search, compare and book flights from 20 airlines offering services to Middlesex County. So buckle up. Your flight to Bradley Intl. Airport (BDL) is ready for boarding with one of these leading carriers:

  • Air Canada - 17 flights to Middlesex County per month
  • JetBlue - 16 flights to Middlesex County per month

What is the best airport to fly to in Middlesex County?
Jet into Hartford, CT (HFD-Hartford - Brainard), the main gateway to Middlesex County. Organizing your flight to this region doesn't get much easier.
How much is a flight to Middlesex County?
The cost for a return flight to Middlesex County this week fluctuated between $82 and $560. If you were traveling one-way from Richmond (RIC), you could have snapped up prices from just $41.
How to book the cheapest flight to Middlesex County?
With some of the most amazing flight deals around, you'll always bag a bargain with Orbitz. The following suggestions will help you find cheap flights to Middlesex County — and leave you with more money to play with:

  • Consider taking off from or landing at other airports to save on your flight. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list your options, if any.
  • If your travel plans aren't set in stone, click on the 'Show flexible dates' option to view the flight deals for a range of departure dates. You may find an amazing fare.
  • To optimize your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird catches the most rewarding savings, so book as soon as you know your travel dates. The cheapest fares get snapped up fast and prices generally rise as the departure date gets closer.
  • Think about bundling your flights, hotels and car rentals into a package with Orbitz to make your dollar go further.
  • Don't travel during peak seasons if possible. By steering clear of school vacations and summer, you can save plenty on your airfare.

What is the best time to book a flight to Middlesex County?
Book in January, February or August for the most competitive fares to Middlesex County. Once you've tracked down a bargain, lock it in — cheap flights tend to appear and vanish at the tap of a button.
What day of the week is the cheapest to book a flight to Middlesex County?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days to book flights to Middlesex County. If you're looking for the best airfares, search across those days and you just might land yourself a terrific flight deal.
What is the cheapest day of the week to fly to Middlesex County?
If you're after cheap flights to Middlesex County, depart at the start of the week. Orbitz data from 2020 shows Monday is the most affordable day to travel, followed by Tuesday. Saturday has the most expensive fares, so avoid this day and do your bank account a favor.
What is the cheapest month to fly to Middlesex County?
To secure cheap flights to Middlesex County, you should pack your bags and take off in August. Orbitz data has found that this is generally a great month to save on your ticket. If you're eager to fly to Middlesex County during June, bear in mind that this is the least affordable time of year to take a trip.
Which airlines allow free cancellation?
Plans change, and we think your ticket should be able to as well. That's why Orbitz makes it a cinch to search for flights with no change fees and free cancellation. Simply enter your departure and arrival destinations and then select "Filter by flexible change policies." How's that for peace of mind?
What do I need for the flight to Middlesex County?
From onboard activities to travel essentials like earplugs, there are a few things a seasoned flyer won't leave home without. To ensure you're organized for your journey, check out this handy list:

  • You'll need to take all relevant travel documents and identification. How much is dependent on where you're taking off from. When you book, you should always use the correct name, gender and birth date listed on your government-issued ID.
  • Stock your carry-on bag with activities and snacks and watch time whiz by on this medium-haul flight. Where possible, jump on the airport's Wi-Fi and download your favorite playlist or podcast to your phone prior to take off.
  • Plane cabins can often get quite cold. If you decide to travel during the peak of the Middlesex County summer, be sure to carry some extra layers of clothing to keep comfortable.

How do I get cheap first-class/business deals to Middlesex County?
If you think a business or first-class fare is out of your price range, think again. Here are some terrific tips to help you score a premium flight to Middlesex County for less:

  • Flexibility is important. By being open to a variety of travel dates, you'll have a better chance of picking up a deal on business or first-class airfares.
  • Find a low-cost carrier that has seats in business class. They often come with more legroom and a glass of Champagne — but without the premium price.
  • Bid for an upgrade in online auctions (if available) or upgrade your seat through your frequent flyer program.

What is the best time to go to Middlesex County?
If you'd like to soak up the unique vibe of Middlesex County in the tourist season, March, May and July are the prime months to visit. June 20 heralds the onset of the summer season in the Northern Hemisphere and is an awesome time to go if you relish the great outdoors. Around this time of the year, average daily temperatures range from 65 ºF to 80 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.